Diethyl Ether → (R)-2-azido-1-benzylethylamine

HRID 1883524Notes

Reaction equation

HRID 1883524 reaction equation
[N:1]([CH2:4][C@H:5]([NH:13]C(OC(C)(C)C)=O)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[N+:2]=[N-:3].CCOCC.[Na+].[Cl-]>Cl.C(O)C.O>[N:1]([CH2:4][C@H:5]([NH2:13])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[N+:2]=[N-:3]

Participants

7

Reactant 3

HCID 3283Diethyl EtherHCID 5234Sodium ChlorideHCID 229417321-azido-2-(R)-(BOC-amino)-3-phenylpropane

Product 1

HCID 14802497(R)-2-azido-1-benzylethylamine

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The compound from step 3 (4.3 g, 15.6 mmol) is dissolved in 30 mL of 4 N HCl in ethanol, and the reaction mixture is stirred for 1.5 hours at room temperature. The solvent is stripped and chased with ether. The residue is dissolved in water, NaCl is added, and the mixture is extracted with ethyl ether, which is discarded. The aqueous layer is adjusted to pH 12 with K2CO3, saturated with NaCl, then extracted with CHCl3. The organic extract is washed with brine, dried (Na2SO4) and filtered. The solvent is removed under vacuumn to afford the title compound.

Workup

  1. extractionthe mixture is extracted with ethyl ether, which
  2. extractionextracted with CHCl3
  3. extractionThe organic extract
  4. washis washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customThe solvent is removed under vacuumn

Sources & evidence

ORD record
ord-8caae4faf503470a8894cd12787cce45
Source dataset
uspto-grants-2004_07
Patent number
US06762168B2

Reaction notes

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